Tetrahydrofuran → 4-(3-Cyanophenyl)-1,4-dihydrobenzo[f]quinoxaline-2,3-dione

HRID 1186721Notes

Reaction equation

HRID 1186721 reaction equation
O1CCCC1.[NH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[NH:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22].[C:26](Cl)(=[O:30])[C:27](Cl)=[O:28]>CO>[C:21]([C:20]1[CH:19]=[C:18]([N:17]2[C:8]3[CH:9]=[CH:10][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:7]=3[NH:6][C:27](=[O:28])[C:26]2=[O:30])[CH:25]=[CH:24][CH:23]=1)#[N:22]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 65578Oxalyl chlorideHCID 679939123-(1-Amino-2-naphthylamino)benzonitrile

Product 1

HCID 566403684-(3-Cyanophenyl)-1,4-dihydrobenzo[f]quinoxaline-2,3-dioneYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an anhydrous tetrahydrofuran (18 mL) solution of 3-(1-amino-2-naphthylamino)benzonitrile (200 mg, 0.771 mmol) was added an anhydrous tetrahydrofuran (2 mL) solution of oxalyl chloride (66 μL, 0.771 mmol) under cooling in an ice-bath. The mixture was stirred under cooling in an ice-bath for 30 minutes and at room temperature for one hour. After addition of methanol (1 mL), the solvent was removed by evaporation under reduced pressure. The mixture was suspended by chloroform, and washed with a saturated aqueous sodium hydrogen carbonate solution. The precipitated solid was collected by filtration, and washed with water. The obtained solid was purified by silica gel chromatography (chloroform/methanol=9/1) to obtain the titled compound as a white powder (23 mg, yield 10%).

Workup

  1. temperatureunder cooling in an ice-bath
  2. customthe solvent was removed by evaporation under reduced pressure
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customThe obtained solid was purified by silica gel chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-f89d5f64634b4d458866e9f6021448d1
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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